Triethylamine → HCID 59735082, compound

HRID 746411Notes

Reaction equation

HRID 746411 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][C@:5]([CH:12]([CH3:14])[CH3:13])([C:8]([O:10][CH3:11])=[O:9])[CH2:4]1.[O:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:12]([C@:5]1([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:7][C@@H:3]([NH:2][CH:18]2[CH2:19][CH2:20][O:15][CH2:16][CH2:17]2)[CH2:4]1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 86606983HCID 86606983, compound

Product 1

HCID 59735082HCID 59735082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (1S,3R)-3-amino-1-isopropylcyclopentanecarboxylate hydrochloride (prepared in the same way as the intermediate from Step F, Procedure A, INTERMEDIATE 2, except with the modification that the methyl ester was employed instead of the benzyl ester, 1.4 g, 6.1 mmol) was combined with tetrahydro-4H-pyran-4-one (730 mg, 7.3 mmol), and triethylamine (1 mL, 7 mmol) in 50 mL of DCM. After 10 min, 4 Å powdered molecular sieves (1 g), and sodium triacetoxyborohydride (5.1 g, 24 mmol) were added and the resulting mixture was permitted to stir overnight. The reaction mixture was filtered through celite, and the filtrate was washed with saturated NaHCO3 solution twice, then once with brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated to afford 1 g of methyl (1S,3R)-1-isopropyl-3-(tetrahydro-2H-pyran-4-ylamino)cyclopentanecarboxylate.

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe filtrate was washed with saturated NaHCO3 solution twice
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10665865e6d140a8a700a80963557506
Source dataset
uspto-grants-2008_07
Patent number
US07393844B2

Reaction notes

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